Pennycress (Thlaspi arvense; field pennycress) is under development as a winter annual oilseed bioenergy crop for the 80 million-acre U.S. Midwest Corn Belt and other temperate regions including the Pacific Northwest. Pennycress has unique attributes such as extreme cold tolerance and rapid spring growth. Off-season integration of domesticated pennycress varieties into existing corn and soybean acres would extend the growing season on established croplands, avoid displacement of food crops, and yield up to 3 billion gallons of seed oil annually. Pennycress oil has a fatty acid composition well suited for conversion to biodiesel and biojet fuel that meets the U.S. Renewable Fuels Standard. Academic, governmental, and industrial stakeholders are working closely to commercialize domesticated pennycress varieties by 2022 that can yield over 1680 kg ha^-1 (1500 lb ac^-1) of seeds producing 600 liters ha^-1 (65 gal ac^-1) of oil annually. However, these first-generation varieties have limited genetic variation, which hampers their adaptability to and resilience against abiotic and biotic challenges. Therefore, crucial work remains to identify genetic variants conferring stress tolerance and resilience for incorporation into next generation elite pennycress varieties. Future pennycress varieties will also require optimized lifespans for a range of latitudes and cropping systems, and improved root architectures and physiologies to maximize water and nutrient scavenging as well as carbon sequestration.